EP4219631A1 - Composition colorante - Google Patents

Composition colorante Download PDF

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Publication number
EP4219631A1
EP4219631A1 EP21872486.2A EP21872486A EP4219631A1 EP 4219631 A1 EP4219631 A1 EP 4219631A1 EP 21872486 A EP21872486 A EP 21872486A EP 4219631 A1 EP4219631 A1 EP 4219631A1
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EP
European Patent Office
Prior art keywords
group
formula
parts
compound
represented
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21872486.2A
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German (de)
English (en)
Inventor
Hitomi MANABE
Yu Takaishi
Sho Tsujiuchi
Manabu Togai
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Dongwoo Fine Chem Co Ltd
Sumika Technology Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Dongwoo Fine Chem Co Ltd
Sumika Technology Co Ltd
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Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd, Dongwoo Fine Chem Co Ltd, Sumika Technology Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of EP4219631A1 publication Critical patent/EP4219631A1/fr
Pending legal-status Critical Current

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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/203—Filters having holographic or diffractive elements
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/36—Amides or imides
    • C08F222/40—Imides, e.g. cyclic imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/36—Amides or imides
    • C08F222/40—Imides, e.g. cyclic imides
    • C08F222/402—Alkyl substituted imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/10—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of amides or imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3415—Five-membered rings
    • C08K5/3417—Five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3462—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41—Compounds containing sulfur bound to oxygen
    • C08K5/42—Sulfonic acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/43—Compounds containing sulfur bound to nitrogen
    • C08K5/435—Sulfonamides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02—Disazo dyes
    • C09B35/021—Disazo dyes characterised by two coupling components of the same type
    • C09B35/03—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound
    • C09B35/031—Disazo dyes characterised by two coupling components of the same type in which the coupling component is a heterocyclic compound containing a six membered ring with one nitrogen atom as the only ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • the present invention relates to a colored composition, a color filter formed from the colored composition, and a display device comprising the color filter.
  • a color filter used for display devices such as a liquid crystal display device, an electroluminescence display device, and a plasma display, and solid-state image sensors such as a CCD sensor and a CMOS sensor is produced from a colored resin composition.
  • a compound represented by formula (x1) is known as a colorant for such a colored resin composition (Patent Document 1).
  • Patent Document 1 JP 2015-61907 (A )
  • a color filter formed from a colored resin composition using the above conventionally known compound may fail to sufficiently satisfy UV ashing resistance.
  • the present invention addresses the problems of providing a colored composition capable of forming a color filter having excellent UV ashing resistance.
  • the gist of the present invention is as follows.
  • a colored composition of the present invention can provide a color filter having excellent UV ashing resistance.
  • the colored composition of the present invention contains a colorant comprising a compound represented by formula (I) (hereinafter, the colorant is sometimes referred to as a colorant (A)) and an alkali soluble resin (hereinafter, sometimes referred to as a resin (B)).
  • a colorant comprising a compound represented by formula (I)
  • a resin hereinafter, sometimes referred to as a resin (B)
  • the colored composition of the present invention preferably further contains a polymerizable compound (hereinafter, sometimes referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (D)).
  • a polymerizable compound hereinafter, sometimes referred to as a polymerizable compound (C)
  • a polymerization initiator hereinafter, sometimes referred to as a polymerization initiator (D)
  • the colored composition of the present invention preferably further contains a solvent (hereinafter, sometimes referred to as a solvent (E)).
  • a solvent hereinafter, sometimes referred to as a solvent (E)
  • the colored composition of the present invention may contain a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)).
  • a leveling agent hereinafter, sometimes referred to as a leveling agent (F)
  • the colorant (A) contains a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)).
  • compound (I) a compound represented by formula (I)
  • the color filter produced has improved UV ashing resistance, and preferably improved UV ashing resistance and improved heat resistance.
  • the compound (I) includes a compound having a resonance structure of formula (I), a tautomer of formula (I), and a compound obtained by rotating each group in formula (I) around a bonding axis of a single bond.
  • the tautomer of formula (I) include a compound represented by formula (I) in which A is a group represented by formula (iia); a compound represented by formula (I) in which B is a group represented by formula (iib); and a compound represented by formula (I) in which A is a group represented by formula (iia) and B is a group represented by formula (iib).
  • X 6 to X 9 and * are the same as mentioned above.
  • substituent A examples include an amino group, an amido group, a carboxyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 alkylthio group, a cyano group, and a halogen atom.
  • the hydrocarbon group represented by X 1 may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group.
  • the aliphatic hydrocarbon group may be saturated or unsaturated and may be chain or cyclic (alicyclic hydrocarbon group).
  • the alicyclic hydrocarbon group may be monocyclic or polycyclic.
  • saturated chain hydrocarbon group examples include straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; and branched-chain alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 1,3-dimethylbutyl, 2-ethylbutyl, and 2-ethylhexyl.
  • straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl
  • branched-chain alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 1,3-dimethylbutyl, 2-ethylbutyl,
  • Examples of the unsaturated chain hydrocarbon group include alkenyl groups such as ethenyl, propenyl (for example, 1-propenyl and 2-propenyl), and butenyl (for example, 1-butenyl and 3-butenyl); and alkynyl groups such as ethynyl, propynyl (for example, 1-propynyl and 2-propynyl), and butynyl (for example, 1-butynyl and 3-butynyl).
  • alkenyl groups such as ethenyl, propenyl (for example, 1-propenyl and 2-propenyl), and butenyl (for example, 1-butenyl and 3-butenyl)
  • alkynyl groups such as ethynyl, propynyl (for example, 1-propynyl and 2-propynyl), and butynyl (for example, 1-butynyl and 3-butynyl).
  • the saturated or unsaturated chain hydrocarbon group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 4 carbon atoms.
  • saturated alicyclic hydrocarbon group examples include cycloalkyl groups such as cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and 2-methylcyclohexyl.
  • Examples of the unsaturated alicyclic hydrocarbon group include cycloalkenyl groups such as cyclohexenyl (for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, and cyclohex-3-en-1-yl), cycloheptenyl, and cyclooctenyl.
  • cyclohexenyl for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, and cyclohex-3-en-1-yl
  • cycloheptenyl for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, and cyclohex-3-en-1-yl
  • cycloheptenyl for example, cyclohex-1-en-1-yl, cyclohex-2-en-1-yl, and cyclohex-3-en-1-yl
  • Examples of the alicyclic hydrocarbon group also include saturated polycyclic hydrocarbon groups such as norbornyl, adamantyl, and bicyclo[2.2.2]octyl; and unsaturated polycyclic hydrocarbon groups such as norbornenyl.
  • the alicyclic hydrocarbon group preferably has 3 to 12 carbon atoms, more preferably 3 to 10 carbon atoms, and still more preferably 3 to 8 carbon atoms.
  • aromatic hydrocarbon group examples include phenyl, o-tolyl, m-tolyl, p-tolyl, 2,4-dimethylphenyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, 2,4-diisopropylphenyl, 2,6-diisopropylphenyl, 4-vinylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 3,5-di(tert-butyl)phenyl, 1-naphthyl, 2-naphthyl, and a group formed by removing one hydrogen atom from tetralin.
  • the aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and still more preferably 6 to 10 carbon atoms.
  • the hydrocarbon group represented by X 1 may be a group obtained by combining two or more of the above-mentioned hydrocarbon groups, and examples thereof include an aralkyl group; an alkyl group to which an alicyclic hydrocarbon group is bonded; an aromatic hydrocarbon group to which a cycloalkyl group is condensed; and an alkyl group to which an aromatic hydrocarbon group to which a cycloalkyl group is condensed is bonded.
  • aralkyl group examples include benzyl, (4-methylphenyl)methyl, and phenethyl.
  • the aralkyl group preferably has 7 to 18 carbon atoms, more preferably 7 to 12 carbon atoms, and still more preferably 7 to 10 carbon atoms.
  • alkyl group to which an alicyclic hydrocarbon group is bonded examples include cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclohexylmethyl, cyclohexylethyl, and adamantylmethyl. This preferably has 4 to 20 carbon atoms, more preferably 4 to 15 carbon atoms, and still more preferably 4 to 10 carbon atoms.
  • Examples of the aromatic hydrocarbon group to which a cycloalkyl group is condensed include a group formed by removing one hydrogen atom from the benzene ring of indan, a group formed by removing one hydrogen atom from the benzene ring of 1-methyl-indan, and a group formed by removing one hydrogen atom from 2-methyl-indan.
  • Examples of the alkyl group to which an aromatic hydrocarbon group to which a cycloalkyl group is condensed is bonded include a group formed by bonding a C 1 -C 4 alkyl group to the benzene ring of indan, a group formed by bonding a C 1 -C 4 alkyl group to the benzene ring of 1-methyl-indan, and a group formed by bonding a C 1 -C 4 alkyl group to the benzene ring of 2-methyl-indan.
  • substituent B examples include an amino group, an amido group, a carboxyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 alkylthio group, a cyano group, a halogen atom, and a hydroxy group.
  • the amino group as the substituent A and the substituent B may be an unsubstituted amino group or a substituted amino group.
  • the substituted amino group preferably has one or two hydrocarbon groups.
  • Examples of the hydrocarbon group include the same groups as those mentioned for the hydrocarbon group represented by X 1 described above, and an alkyl group is preferred.
  • the hydrocarbon group has preferably 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms.
  • substituted amino group examples include N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-diethylamino, N-propylamino, N,N-dipropylamino, N-isopropylamino, N,N-diisopropylamino, N-phenylamino, N,N-diphenylamino, and N,N-ethylmethylamino.
  • the amido group as the substituent A and the substituent B means a group obtained by removing one hydrogen atom bonded to a nitrogen atom in an amide.
  • the amide group include formamide, acetamide, propylamide, butylamide, benzamide, trifluoroacetamide, and pentafluorobenzamide.
  • the amide group preferably has 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms, and still more preferably 2 to 6 carbon atoms.
  • alkoxy group as the substituent A and the substituent B examples include methoxy, ethoxy, propoxy, n-butoxy, and tert-butoxy.
  • the alkoxy group preferably has 1 to 4 carbon atoms and more preferably 1 or 2 carbon atoms.
  • alkylthio group examples include methylthio, ethylthio, propylthio, and n-butylthio.
  • the alkylthio group preferably has 1 to 4 carbon atoms and more preferably 1 or 2 carbon atoms.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • a fluorine atom, a chlorine atom, or a bromine atom is preferable, and a chlorine atom is more preferable.
  • X 1 is preferably a C 1 -C 10 alkyl group, a C 1 -C 4 alkoxy group, a cyano group, or a halogen atom, and more preferably a C 1 -C 4 alkyl group, a C 1 -C 4 alkoxy group, a cyano group, or a halogen atom.
  • n is preferably an integer of 0 to 2.
  • n is an integer of 2 or more, a plurality of X 1 s may be the same or different.
  • X 1 s bonded to adjacent carbon atoms may be combined with each other to form a ring.
  • Examples of the ring formed by combining X 1 s bonded to adjacent carbon atoms with each other include rings represented by the following formulas. In the formulas, * indicates a point of attachment to each of adjacent carbon atoms on the phenylene group in formula (ph1).
  • formula (ph1) preferably has points of attachment to A and B at the 1st and 4th positions from the viewpoint of availability of raw materials.
  • L 1 in the compound (I) is preferably a group represented by formula (ph2).
  • X 2 to X 5 each independently represent a hydrogen atom, a C 1 -C 4 alkyl group, an amino group, an amido group, a carboxyl group, a C 1 -C 4 alkoxy group, a C 1 -C 4 alkylthio group, a cyano group, or a halogen atom.
  • X 2 and X 3 , and X 4 and X 5 may be combined with each other to form a ring.
  • * represents a point of attachment to A
  • ** represents a point of attachment to B.
  • Examples of the C 1 -C 4 alkyl group represented by X 2 to X 6 include methyl, ethyl, propyl, n-butyl, isobutyl, and tert-butyl. Among these, methyl or ethyl is preferable.
  • Examples of the amino group represented by X 2 to X 5 include the groups described as the amino group as the substituent A and the substituent B, and the preferred mode is also the same.
  • amido group represented by X 2 to X 5 examples include the groups described as the amido group as the substituent A and the substituent B, and the preferred mode is also the same.
  • Examples of the alkoxy group represented by X 2 to X 5 include the groups described as the alkoxy group as the substituent A and the substituent B, and the preferred mode is also the same.
  • alkylthio group represented by X 2 to X 5 examples include the groups described as the alkylthio group as the substituent A and the substituent B, and the preferred mode is also the same.
  • halogen atom represented by X 2 to X 5 examples include the atoms described as the halogen atom as the substituent A and the substituent B, and the preferred mode is also the same.
  • Examples of the ring formed by combining X 2 and X 3 , and X 4 and X 5 with each other include the rings described as the ring formed by combining X 1 s with each other.
  • the group represented by formula (ph2) is preferably any of groups represented by formulas (ph2-1) to (ph2-12), and more preferably any of groups represented by formulas (ph2-1) to (ph2-11).
  • * represents a point of attachment to A
  • ** represents a point of attachment to B.
  • Examples of the hydrocarbon group represented by X 6 to X 9 in formulas (ia) and (ib) include the groups described as the hydrocarbon group represented by X 1 mentioned above.
  • -CH 2 - contained in the hydrocarbon group represented by X 6 to X 9 may be replaced with -O-, -CO-, or -NH-
  • -C ⁇ contained in the hydrocarbon group represented by X 6 to X 9 may be replaced with -N ⁇ .
  • X 6 and X 7 may be combined with each other to form a ring
  • X 8 and X 9 may be combined with each other to form a ring.
  • Examples of a group obtained by combining X 6 and X 7 with each other to form a ring in formula (ia) and a group obtained by combining X 8 and X 9 with each other to form a ring in formula (ib) include groups represented by the following formulas.
  • * represents a point of attachment to L 1 .
  • At least one hydrogen atom in the group represented by each of the following formulas may be replaced with substituent C described below.
  • substituent C examples include a hydroxy group, a C 1 -C 4 alkoxy group, a C 1 -C 4 alkylthio group, a carboxyl group, an amino group, an amide group, a cyano group, a halogen atom, -SO 3 H, -SO 3 M, -SO 3 T 0.5 , and -SO 2 N(R 17 ) 2 .
  • M represents an alkali metal atom
  • T represents an alkaline-earth metal atom
  • R 17 represents a hydrogen atom or a hydrocarbon group.
  • alkoxy group as the substituent C examples include the groups described as the alkoxy group as the substituent A and the substituent B, and the preferred mode is also the same.
  • alkylthio group as the substituent C examples include the groups described as the alkylthio group as the substituent A and the substituent B, and the preferred mode is also the same.
  • amino group as the substituent C examples include the groups described as the amino group as the substituent A and the substituent B, and the preferred mode is also the same.
  • Examples of the amide group as the substituent C include the groups described as the amide group as the substituent A and the substituent B, and the preferred mode is also the same.
  • halogen atom as the substituent C examples include the atoms described as the halogen atom as the substituent A and the substituent B. Among these, a chlorine atom, a bromine atom, and a fluorine atom are preferable.
  • Examples of the alkali metal atom represented by M include sodium and potassium.
  • Examples of the alkaline-earth metal atom represented by T include magnesium, calcium, and barium.
  • the compound (I) has the following structure.
  • L 1 , A, B, and T have the same meanings as above; and -SO 3 - substitutes for any of the hydrogen atoms in the hydrocarbon group represented by X 6 to X 9 in A and B.
  • R 17 represents a hydrogen atom or a hydrocarbon group. Two R 17 s may be the same or different, and it is preferable that one be a hydrogen atom and the other be a hydrocarbon group.
  • Examples of the hydrocarbon group represented by R 17 include the groups described as the hydrocarbon group represented by X 1 mentioned above. Among these, a C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a C 3 -C 12 saturated polycyclic hydrocarbon group, or a C 6 -C 18 aromatic hydrocarbon group are preferable.
  • the group represented by formula (ia) and the group represented by formula (ib) are preferably the same. That is, it is preferable that X 6 and X 8 represent the same group, and X 7 and X 9 represent the same group. When these groups are the same, the color filter produced has an improved color density.
  • the group represented by formula (ia) and the group represented by formula (ib) are each independently more preferably any of groups represented by formulas (t1) to (t5), still more preferably any of groups represented by formulas (t1) to (t4), and particularly preferably any of groups represented by formulas (t1) to (t3).
  • R 1 to R 16 each independently represent a hydrogen atom, a hydrocarbon group optionally having a substituent, a heterocyclic group, a cyano group, or a halogen atom; and * represents a point of attachment to L 1 .
  • Examples of the hydrocarbon group represented by R 1 to R 16 include the groups described as the hydrocarbon group represented by X 1 mentioned above. Among these, a C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, and a C 6 -C 12 aromatic hydrocarbon group are preferable, and a C 1 -C 6 alkyl group, a C 3 -C 8 cycloalkyl group, and a phenyl group are more preferable.
  • Examples of the substituent that the hydrocarbon group represented by R 1 to R 16 optionally has include the groups described as the substituent C, and the preferred mode is also the same.
  • heterocyclic group represented by R 1 to R 16 examples include thienyl, benzo[b]thienyl, thianthrenyl, furyl, pyranyl, isobenzofuranyl, chromenyl, xanthenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, indolyl, 1H-indazolyl, isoquinolyl, quinolyl, phthalazinyl, carbazolyl, acridinyl, chromanyl, pyrrolidinyl, piperidyl, piperazinyl, indolinyl, isoindolinyl, and benzimidazolonyl.
  • a heterocyclic group having a benzene ring such as benzo[b] thienyl, thianthrenyl, isobenzofuranyl, chromenyl, xanthenyl, indolyl, 1H-indazolyl, isoquinolyl, quinolyl, phthalazinyl, carbazolyl, acridinyl, chromanyl, indolinyl, isoindolinyl, and benzimidazolonyl are preferable; and indolyl, 1H-indazolyl, isoquinolyl, quinolyl, phthalazinyl, carbazolyl, acridinyl, indolinyl, isoindolinyl, and benzimidazolonyl are more preferable.
  • Examples of the halogen atom represented by R 1 to R 16 include the atoms described as the halogen atom as the substituent A and the substituent B. Among these, a chlorine atom and a fluorine atom are preferable.
  • R 1 is preferably an aromatic hydrocarbon group optionally having a substituent, more preferably a phenyl group optionally having a substituent, still more preferably a phenyl group optionally having a substituent at the para position, still further preferably a phenyl group optionally having a halogen atom, -SO 3 H, -SO 3 T 0.5 , -SO 3 M, or -SO 2 N(R 17 ) 2 at the para position, and particularly preferably a phenyl group optionally having a halogen atom, -SO 3 H, or -SO 2 N(R 17 ) 2 at the para position.
  • R 2 is preferably an alkyl group optionally having a substituent, more preferably an alkyl group optionally having a halogen atom, and still more preferably a C 1 -C 4 alkyl group optionally having a halogen atom.
  • R 3 and R 4 are each independently preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aromatic hydrocarbon group, and more preferably a hydrogen atom, a C 1 -C 4 alkyl group, a C 3 -C 8 cycloalkyl group, or a phenyl group. R 3 and R 4 are preferably the same.
  • R 5 is preferably a hydrogen atom or an alkyl group optionally having a substituent, more preferably an alkyl group, and still more preferably a C 1 -C 4 alkyl group.
  • R 6 is preferably a cyano group or an alkyl group optionally having a substituent, more preferably a cyano group or an alkyl group optionally having a halogen atom, and still more preferably a cyano group or a C 1 -C 4 alkyl group optionally having a halogen atom.
  • R 7 is preferably an alkyl group optionally having a substituent, more preferably an alkyl group optionally having a halogen atom, and still more preferably a C 1 -C 4 alkyl group optionally having a halogen atom.
  • R 8 is preferably an alkyl group optionally having a substituent, and more preferably a C 1 -C 4 alkyl group.
  • R 9 is preferably a hydrogen atom or an alkyl group optionally having a substituent, and more preferably a hydrogen atom or a C 1 -C 4 alkyl group.
  • R 10 is preferably an aromatic hydrocarbon group optionally having a substituent or a heterocyclic group, more preferably a phenyl group optionally having a substituent or a heterocyclic group having a benzene ring, and still more preferably a phenyl group optionally having a halogen atom or a benzimidazolonyl group.
  • R 11 to R 16 are each independently preferably a hydrogen atom or an alkyl group optionally having a substituent, more preferably a hydrogen atom or an alkyl group optionally having a halogen atom, and still more preferably a hydrogen atom or a C 1 -C 4 alkyl group optionally having a halogen atom.
  • Examples of compound (I) include compounds (AI-1) to (AI-748) shown in Tables 1 to 7. [Table 1] L 1 A B L 1 A B L 1 A B AI-1 ph3 t6 t6 AI-41 ph3 t9 t12 AI-81 ph4 t6 t10 AI-2 ph3 t7 t7 AI-42 ph3 t9 t13 AI-82 ph4 t6 t11 AI-3 ph3 t8 t8 AI-43 ph3 t9 t14 AI-83 ph4 t6 t12 AI-4 ph3 t9 t9 AI-44 ph3 t9 t15 AI-84 ph4 t6 t13 AI-5 ph3 t10 t10 AI-45 ph3 t9 t16 AI-85 ph4 t6 t14 AI-6 ph3 t11 t11 AI-46 ph3 t10
  • ph3 to ph10 represent groups represented by formulas (ph3) to (ph10), respectively.
  • * represents a point of attachment to A
  • ** represents a point of attachment to B.
  • t6 to t16 represent groups represented by formulas (t6) to (t16), respectively.
  • R 18 represents 2-methylcyclohexyl, phenyl, 3,5-di-tert-butylphenyl, adamantyl, or 1,3-dimethylbutyl. * represents a point of attachment to L 1 .
  • Examples of compound (I) also include following compounds (AI-749) to (AI-753).
  • compounds (AI-1) to (AI-682) and (AI-749) to (AI-753) are preferable,
  • the compound (I) can be produced, for example, by the following method.
  • compound (I) is a compound represented by formula (I') (hereinafter sometimes referred to as compound (I'))
  • an amine represented by formula (pt1) is diazotized to produce a diazonium salt represented by formula (q1).
  • the produced diazonium salt is reacted with a compound represented by formula (pt2) to produce a compound represented by formula (q2).
  • the compound represented by formula (q2) is reduced to produce an amine represented by formula (q3).
  • the produced amine is diazotized to produce a diazonium salt represented by formula (q4), and the produced diazonium salt is then reacted with a compound represented by formula (pt3), whereby a compound represented by formula (I') can be produced.
  • the diazonium salt represented by formula (q!) can be obtained, for example, by diazotization of the amine represented by formula (pt1) with a nitrous acid, a nitrous acid salt, or a nitrous acid ester. Such diazotization can be carried out by any known method.
  • Examples of the inorganic anion include a fluoride ion, a chloride ion, a bromide ion, an iodide ion, a perchlorate ion, and a hypochlorite ion.
  • Examples of the organic anion include CH 3 COO - and C 6 H 5 COO - .
  • Preferred examples of Q 1 and Q 2 include a chloride ion, a bromide ion, and CH 3 COO - .
  • An acidic catalyst may be used in the foregoing diazotization reaction to allow the reaction to proceed smoothly.
  • Examples of the acidic catalyst include mineral acids such as sulfuric acid and hydrochloric acid.
  • the compound represented by formula (q2) can be produced by diazo-coupling the diazonium salt represented by formula (q!) with the compound represented by formula (pt2).
  • diazo-coupling can be carried out by any known method.
  • This reaction is preferably performed in the presence of an aqueous solvent.
  • the aqueous solvent include water, a water-soluble organic solvent such as methanol, ethanol, propanol, and 2-propanol, and a mixed solvent of water and the water-soluble organic solvent.
  • a mixed solvent of water and the water-soluble organic solvent is preferable.
  • the compound represented by formula (q3) can be produced by reduction of the compound represented by the formula (q2).
  • the method of reduction is not particularly limited, and the reduction can be carried out by any known method.
  • reduction with a reducing agent such as a sulfide can be employed.
  • the sulfide is not particularly limited, and examples thereof include hydrosulfides such as sodium hydrosulfide, potassium hydrosulfide, and ammonium hydrosulfide, and sulfides such as sodium sulfide, potassium sulfide and ammonium sulfide. These hydrosulfides and sulfides may be anhydrous or contain water of crystallization.
  • the reduction reaction is preferably performed in the presence of an aqueous solvent.
  • the aqueous solvent include the same solvents as the above-mentioned aqueous solvents, and preferred is water.
  • the diazonium salt represented by formula (q4) can be obtained by diazotization of the amine represented by formula (q3).
  • the method of diazotization the same method as the above-mentioned method of diazotization of the compound represented by formula (pt1) can be employed.
  • the compound (I') can be produced by diazo-coupling the diazonium salt represented by formula (q4) with the compound represented by formula (pt3).
  • the method of diazo-coupling the same method as the above-mentioned method of diazo-coupling of the diazonium salt represented by formula (q1) with the compound represented by formula (pt2) can be employed.
  • the compound (I) in which at least one of X 6 to X 9 is a hydrocarbon group having -SO 3 M or -SO 3 T 0.5 as a substituent (hereinafter sometimes referred to as compound (I"))
  • the compound (I') in which at least one of X 6p to X 9p is a hydrocarbon group having a sulfonic acid group as a substituent is produced by the method described above, and then the produced compound (I') having a sulfonic acid group as a substituent is reacted with an alkali metal salt or an alkaline-earth metal salt.
  • the sulfonic acid group in the compound (I') is converted to -SO 3 M or -SO 3 T 0.5 , whereby a compound (I") can be produced.
  • Examples of the alkali metal compound and the alkaline-earth metal compound include a salt with a chloride ion, a salt with an iodide ion, a salt with a bromide ion, a salt with an acetate ion, a salt with a formate ion, and a salt with a benzoate ion.
  • a salt with an acetate ion is preferable.
  • This reaction is preferably performed in the presence of a mixed solvent of an organic solvent and an aqueous solvent.
  • aqueous solvent include the same solvents as the above-mentioned aqueous solvents, and preferred is water.
  • the organic solvent include ester solvents such as ethyl lactate, butyl lactate, n-butyl acetate, ethyl butyrate, and methyl acetoacetate; ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, and propylene glycol monomethyl ether; ketone solvents such as diacetone alcohol; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; and halogen solvents such as chloroform and methylene chloride.
  • amide solvents are preferable.
  • compound (I′′′) When producing a compound represented by the compound (I) in which at least one of X 6 to X 9 is a hydrocarbon group having -SO 2 N(R 17 ) 2 as a substituent (hereinafter sometimes referred to as compound (I′′′)), first, the compound (I') in which at least one of X 6p to X 9p is a hydrocarbon group having a sulfonic acid group as a substituent is produced by the method described above, and then the produced compound (I') having a sulfonic acid group is reacted with a halogenating agent. To the resulting reaction solution are added a base and NH(R 17 ) 2 to allow them to react. Through this reaction, the sulfonic acid group in the compound (I') is converted to -SO 2 N(R 17 ) 2 , whereby a compound (I′′′) can be produced.
  • compound (I′′′) When producing a compound represented by the compound (I) in which at least one
  • halogenating agent examples include thionyl chloride, oxalyl chloride, phosphorus trichloride, and phosphorus pentachloride.
  • the reaction is preferably performed in the presence of an organic solvent.
  • organic solvent include the same solvents as the above-mentioned organic solvents, and preferred are amide solvents and halogen solvents.
  • the base examples include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organometallic compounds such as butyllithium, tert-butyllithium and phenyllithium; and inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
  • organic bases are preferable.
  • the method of obtaining the compound (I) for example, compounds (I') to (I′′′) from the reaction mixture
  • various known methods can be employed.
  • an acid acetic acid or the like
  • precipitated crystal can be collected by filtration.
  • the solvent is distilled off from the reaction mixture after completion of the reaction, a small amount of methanol is added, followed by stirring, and an acid (acetic acid or the like) and water is added to the resulting solution, whereby precipitated crystal can be collected by filtration.
  • the crystal obtained by filtration is preferably washed with water or methanol and then dried. If necessary, the crystal may be further purified by a known method such as recrystallization.
  • the content of the compound (I) in the whole amount of the colorant (A) is preferably 5% by mass or more, more preferably 10% by mass or more, and still more preferably 20% by mass or more. This content may 100% by mass and may 98% by mass or less or 93% by mass or less.
  • the colorant (A) may further contain a colorant different from the compound (I).
  • the colorant different from the compound (I) may be one or both of a dye (hereinafter, sometimes referred to as a dye (A1)) and a pigment (hereinafter, sometimes referred to as a pigment (A2)).
  • the dye (A1) is not particularly limited, and any known dye other than the compound (I) can be used.
  • Examples of the dye (A1) include a solvent dye, an acid dye, a direct dye, and a mordant dye.
  • Examples of the dye (A1) include a compound that is not a pigment but classified into a compound having a hue in the Color Index (published by The Society of Dyers and Colourists ), and a known dye as described in Dying note (Shikisensha Co., Ltd.).
  • examples thereof include an azo dye other than the compound (I), a cyanine dye, a triphenylmethane dye, a xanthene dye, a phthalocyanine dye, an anthraquinone dye, a naphthoquinone dye, a quinonimine dye, a methine dye, an azomethine dye, a squarylium dye, an acridine dye, a styryl dye, a coumarin dye, a quinoline dye, and a nitro dye.
  • a dye which is soluble in an organic solvent is preferable.
  • dye (A1) examples include
  • dye (A1) also include compounds represented formulas (z) and (z1).
  • These dyes may be appropriately selected depending on the optical spectrum of a desired color filter.
  • the content of the dye (A1) is preferably 1% by mass or more, more preferably 3% by mass or more, and still more preferably 5% by mass or more, and is preferably 20% by mass or less and more preferably 15% by mass or less, in the whole amount of the colorant (A).
  • the pigment (A2) is not particularly limited, and any known pigment can be used.
  • Examples of the pigment (A2) include a pigment that is classified into a pigment in the Color Index (published by The Society of Dyers and Colourists ).
  • the pigment may be subjected to a treatment such as a rosin treatment; a surface treatment using a pigment derivative or the like having an introduced acidic group or basic group; a pigment surface graft treatment with a polymeric compound or the like; a particle micronization treatment by a sulfuric acid micronization method or the like; a washing treatment with an organic solvent, water or the like for removing impurities; or a removing treatment of ionic impurities by an ionic exchange method or the like.
  • a treatment such as a rosin treatment; a surface treatment using a pigment derivative or the like having an introduced acidic group or basic group; a pigment surface graft treatment with a polymeric compound or the like; a particle micronization treatment by a sulfuric acid micronization method or the like; a washing treatment with an organic solvent, water or the like for removing impurities; or a removing treatment of ionic impurities by an ionic exchange method or the like.
  • the pigment preferably has a uniform particle diameter.
  • a pigment dispersant is added, followed by performing a dispersion treatment, whereby a pigment dispersion in which the pigment is uniformly dispersed in a solvent can be produced.
  • pigment dispersant examples include surfactants such as a cationic surfactant, an anionic surfactant, a non-ionic surfactant, an amphoteric surfactant, a polyester-based surfactant, a polyamine-based surfactant, and an acrylic surfactant. These pigment dispersants may be used singly or in combination of two or more thereof.
  • pigment dispersant examples include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Flowlen (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Zeneca Ltd.), EFKA (manufactured by Ciba), AJISPER (manufactured by Ajinomoto Fine-Techno Co., Inc.), and Disperbyk (manufactured by BYK-Chemie Corporation).
  • the amount thereof used is preferably 1% by mass or more and 100% by mass or less, and more preferably 5% by mass or more and 50% by mass or less, relative to the whole amount of the pigment (A2).
  • the amount of the pigment dispersant used falls within the above-mentioned range, a pigment dispersion in which two or more pigments are more uniformly dispersed tends to be obtained.
  • the content of the colorant (A) is preferably 0.1% by mass or more and 70% by mass or less, more preferably 0.5% by mass or more and 60% by mass or less, and still more preferably 1% by mass or more and 50% by mass or less, in the whole amount of the solid content.
  • the content of the colorant (A) falls within the above-mentioned range, the color density of the resulting color filter is sufficient, and the composition can be made to contain a required amount of the resin (B) and polymerizable compound (C), so that it is possible to form a pattern having sufficient mechanical strength.
  • the term "whole amount of the solid content” means the total amount of components obtained by excluding the solvent from the colored composition of the present invention.
  • the whole amount of the solid content and the content of each of the components with respect thereto can be measured by known analysis means such as liquid chromatography or gas chromatography.
  • the resin (B) is an alkali soluble resin.
  • Examples of the resin (B) include the following resins [K1] to [K6].
  • (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m- or p-vinylbenzoic acid;
  • acrylic acid, methacrylic acid, maleic anhydride and the like are preferable.
  • (meth)acrylic acid represents at least one selected from the group consisting of acrylic acid and methacrylic acid.
  • (meth)acryloyl "(meth)acrylate” and the like also have similar meanings.
  • (b) means a polymerizable compound having a C 2 -C 4 cyclic ether structure (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond.
  • (b) is preferably a monomer having a C 2 -C 4 cyclic ether and a (meth)acryloyloxy group.
  • Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter, the monomer (b1) is sometimes referred to as "(b1)"), a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, the monomer (b2) is sometimes referred to as "(b2)"), and a monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, the monomer (b3) is sometimes referred to as "(b3)").
  • a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond hereinafter, the monomer (b1) is sometimes referred to as "(b1)"
  • a monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond hereinafter, the
  • Examples of (b1) include a monomer (b1-1) having a structure where a straight- or branched-chain aliphatic unsaturated hydrocarbon is epoxidized (hereinafter, the monomer (b1-1) is sometimes referred to as "(b1-1)") and a monomer (b1-2) having a structure where an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter, sometimes referred to as "(b1-2)").
  • (b1-1) examples include glycidyl(meth)acrylate, ⁇ -methylglycidyl(meth)acrylate, ⁇ -ethylglycidyl(meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, ⁇ -methyl-o-vinylbenzyl glycidyl ether, ⁇ -methyl-m-vinylbenzyl glycidyl ether, ⁇ -methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxy
  • (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide 2000 manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl(meth)acrylate (for example, Cyclomer A400 manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl(meth)acrylate (for example, Cyclomer M100 manufactured by Daicel Corporation), a compound represented by formula (R1), and a compound represented by formula (R2).
  • Examples of the C 1 -C 4 alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl.
  • alkyl group in which the hydrogen atom is replaced with the hydroxy group examples include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl, 1-hydroxy-1-methylethyl, 2-hydroxy-1-methylethyl, 1-hydroxybutyl, 2-hydroxybutyl, 3-hydroxybutyl, and 4-hydroxybutyl.
  • R ra and R rb are preferably a hydrogen atom, methyl, hydroxymethyl, 1-hydroxyethyl, or 2-hydroxyethyl, and more preferably a hydrogen atom or methyl.
  • alkanediyl group examples include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl.
  • X ra and X rb are preferably a single bond, methylene, ethylene, *-CH 2 -O-, or *-CH 2 CH 2 -O-, and more preferably a single bond or *-CH 2 CH 2 -O- (* represents a point of attachment to O).
  • Examples of the compound represented by formula (R1) include a compound represented by any of formulas (R1-1) to (R1-15).
  • the compound represented by any of formulas (R1-1), (R1-3), (R1-5), (R1-7), (R1-9), and (R1-11) to (R1-15) is preferable, and the compound represented by any of formulas (R1-1), (R1-7), (R1-9), and (R1-15) is more preferable.
  • Examples of the compound represented by formula (R2) include a compound represented by any of formulas (R2-1) to (R2-15).
  • the compound represented by any of formulas (R2-1), (R2-3), (R2-5), (R2-7), (R2-9), and (R2-11) to (R2-15) is preferable, and the compound represented by any of formulas (R2-1), (R2-7), (R2-9), and (R2-15) is more preferable.
  • the compound represented by formula (R1) and the compound represented by formula (R2) may be used singly or in combinations of two or more thereof.
  • the content ratio thereof [compound represented by formula (R1): compound represented by formula (R2)] is preferably 5:95 to 95:5, and more preferably 20:80 to 80:20, on a molar basis.
  • (b2) is more preferably a monomer having an oxetanyl group and a (meth)acryloyloxy group.
  • Examples of (b2) include 3-methyl-3-methacryloyloxy methyl oxetane, 3-methyl-3-acryloyloxy methyl oxetane, 3-ethyl-3-methacryloyloxy methyl oxetane, 3-ethyl-3-acryloyloxy methyl oxetane, 3-methyl-3-methacryloyloxy ethyl oxetane, 3-methyl-3-acryloyloxy ethyl oxetane, 3-ethyl-3-methacryloyloxy ethyl oxetane, and 3-ethyl-3-acryloyloxy ethyl oxetane.
  • (b3) is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group.
  • Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150 manufactured by Osaka Organic Chemical Industry Ltd.) and tetrahydrofurfuryl methacrylate.
  • (b) is preferably (b1) since reliabilities such as heat resistance and chemical resistance of a color filter to be produced can be further improved, and more preferably (b1-2) since the storage stability of the colored composition is excellent.
  • styrene vinyltoluene
  • N-phenylmaleimide N-cyclohexylmaleimide
  • N-benzylmaleimide bicyclo[2.2.1]hept-2-ene
  • 2-hydroxyethyl(meth)acrylate and the like are preferable.
  • the ratio of the structural unit derived from each of (a) and (b) in the total structural units constituting the resin [K1] is preferably the following:
  • the resin [K1] can be produced with reference to the method described in, for example, a document " Experimental Method for Polymer Synthesis” (edited by Takayuki Otsu, published by Kagaku-Dojin Publishing Co., Ltd., First Edition, First Printed on Mar. 1, 1972 ) and cited documents described in the document.
  • the producing method of the resin [K1] include the following method: predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like are placed in a reaction vessel, a deoxidization atmosphere is formed by, for example, substituting oxygen with nitrogen, and these are heated and kept warm during stirring.
  • the polymerization initiator, the solvent, and the like used here are not particularly limited, and those commonly used in the art can be used.
  • the polymerization initiator include azo compounds such as 2,2'-azobisisobutyronitrile and 2,2'-azobis(2,4-dimethylvaleronitrile, and organic peroxides such as benzoyl peroxide.
  • the solvent is required to dissolve each monomer, and examples thereof include solvents described later as the solvent (E).
  • the obtained copolymer may be used directly in the form of a solution after reaction.
  • a solution obtained by concentrating or diluting the solution after reaction may be used, or a solid (powder) taken out from the solution after reaction by a method such as reprecipitation may be used.
  • the solution after reaction can be used directly in the preparation of the colored composition by using a solvent contained in the colored composition as the solvent for the polymerization, whereby the producing process of the colored composition can be simplified.
  • the ratio of the structural unit derived from each of (a) to (c) in the total structural units constituting the resin [K2] is preferably the following:
  • the resin [K2] can be produced in a similar manner to the producing method of the resin [K1], for example.
  • the ratio of the structural unit derived from each of (a) and (c) in the total structural units constituting the resin [K3] is preferably the following:
  • the resin [K3] can be produced in a similar manner to the producing method of the resin [K1], for example.
  • the resin [K4] can be produced by producing a copolymer of (a) and (c) and then adding a C 2 -C 4 cyclic ether contained in (b) to a carboxylic acid and/or a carboxylic anhydride contained in (a).
  • the copolymer of (a) and (c) is produced in a similar manner to the producing method of the resin [K1].
  • the ratio of the structural unit derived from each of (a) and (c) is preferably the same ratio as that described in the resin [K3].
  • the amount of (b) used is preferably 5 to 80 mol, and more preferably 10 to 75 mol, relative to 100 mol of (a).
  • amount of (b) used falls within the above-mentioned range, there is a tendency that the storage stability of the colored composition, the developability thereof during the formation of a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the pattern obtained are good. Since the reactivity of the cyclic ether is high, and the unreacted (b) is less likely to remain, (b) used for the resin [K4] is preferably (b1), and more preferably (b1-1).
  • the amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b), and (c).
  • the amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b), and (c).
  • Reaction conditions such as a feeding method, a reaction temperature, and time can be appropriately adjusted in consideration of a production equipment, an amount of heat generation due to polymerization, and the like.
  • the feeding method and the reaction temperature can be appropriately adjusted like the polymerization conditions.
  • a producing method of the resin [K5] contains a step of producing a copolymer of (b) and (c) in a similar manner to the producing method of the resin [K1] as a first step.
  • the obtained copolymer may be used directly in the form of a solution after reaction.
  • a solution obtained by concentrating or diluting the solution after reaction may be used, or a solid (powder) taken out from the solution after reaction by a method such as reprecipitation may be used.
  • the ratio of the structural unit derived from each of (b) and (c) relative to the total number of moles of the total structural units constituting the copolymer is preferably the following:
  • the producing method of the resin [K5] further contains a step of reacting a carboxylic acid or a carboxylic anhydride contained in (a) with the cyclic ether derived from (b) contained in the copolymer of (b) and (c) under the same conditions as those of the producing method of the resin [K4], whereby the resin [K5] can be produced.
  • the amount of (a) used that is reacted with the copolymer is preferably 5 to 80 mol relative to 100 mol of (b). Since the reactivity of the cyclic ether is high, and the unreacted (b) is less likely to remain, (b) used for the resin [K5] is preferably (b1), and more preferably (b1-1).
  • the resin [K6] is a resin produced by further reacting a carboxylic anhydride with the resin [K5].
  • the carboxylic anhydride is reacted with a hydroxy group generated by the reaction between the cyclic ether and the carboxylic acid or a carboxylic anhydride.
  • carboxylic anhydride examples include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride.
  • the amount of the carboxylic anhydride used is preferably 0.5 to 1 mol relative to 1 mol of the amount of (a) used.
  • the resin (B) include a resin [K1] such as a 3,4-epoxycyclohexylmethyl(meth)acrylate/(meth)acrylic acid copolymer or a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate/(meth)acrylic acid copolymer; a resin [K2] such as a glycidyl(meth)acrylate/benzyl(meth)acrylate/(meth)acrylic acid copolymer, a glycidyl(meth)acrylate/styrene/(meth)acrylic acid copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, a 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl acrylate/(meth)acrylic acid/N
  • the resin (B) is preferably at least one selected from the group consisting of the resin [K1] and the resin [K2], and more preferably the resin [K2].
  • the weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 or more and 100,000 or less, more preferably 5,000 or more and 50,000 or less, and still more preferably 5,000 or more and 30,000 or less.
  • the molecular weight falls within the above-mentioned range, there is a tendency that the hardness of the color filter is improved, that the residual film ratio is increased, that the solubility of an unexposed area by a developing solution becomes good, and that the resolution of a colored pattern is improved.
  • the degree of dispersion [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 or more and 6 or less, and more preferably 1.2 or more and 4 or less.
  • the acid value of the resin (B) is preferably 50 mg-KOH/g or more and 170 mg-KOH/g or less, more preferably 60 mg-KOH/g or more and 150 mg-KOH/g or less, and still more preferably 70 mg-KOH/g or more and 135 mg-KOH/g or less, in terms of solid content.
  • the acid value is a value which is measured as an amount (mg) of potassium hydroxide required for neutralizing 1 g of the resin (B), and which can be determined by, for example, titration with an aqueous potassium hydroxide solution.
  • the content of the resin (B) is preferably 7% by mass or more and 85% by mass or less, more preferably 13% by mass or more and 80% by mass or less, and still more preferably 15% by mass or more and 70% by mass or less, relative to the whole amount of the solid content.
  • the content of the resin (B) falls within the above-mentioned range, there is a tendency that the colored pattern can be formed, and that the resolution of the colored pattern and the residual film ratio are improved.
  • the polymerizable compound (C) is a compound capable of being polymerized by the action of an active radical and/or an acid generated from the polymerization initiator (D).
  • Examples of the polymerizable compound (C) include a compound having a polymerizable ethylenically unsaturated bond, and a (meth)acrylic acid ester compound is preferable.
  • the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds.
  • a polymerizable compound include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified
  • the polymerizable compound (C) is preferably at least one selected from the group consisting of dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.
  • the weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.
  • the content of the polymerizable compound (C) is preferably 5% by mass or more and 75% by mass or less, more preferably 7% by mass or more and 70% by mass or less, and still more preferably 15% by mass or more and 70% by mass or less, relative to the whole amount of the solid content.
  • the content of the polymerizable compound (C) falls within the above-mentioned range, there is a tendency that the residual film ratio during the formation of the colored pattern and the chemical resistance of the color filter are improved.
  • the polymerization initiator (D) is not particularly limited, as long as the polymerization initiator (D) is a compound capable of generating active radicals, an acid or the like by the action of light or heat to initiate polymerization. Any known polymerization initiator can be used.
  • Examples of the polymerization initiator capable of generating active radicals include an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound.
  • the O-acyloxime compound is a compound having a partial structure represented by formula (d1).
  • * represents a point of attachment.
  • O-acyloxime compound examples include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6- ⁇ 2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl ⁇ -9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-
  • the O-acyloxime compound is preferably at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine; and more preferably N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexyl
  • the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2) or (d3).
  • the benzene ring optionally has a substituent.
  • Examples of the compound having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl] -1- [4-(4-morpholinyl)phenyl]butane-1-one.
  • Commercially available products such as Irgacures 369, 907, and 379 (all manufactured by BASF Corporation) may be used.
  • Examples of the compound having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenylketone, an oligomer of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, ⁇ , ⁇ -diethoxyacetophenone, and benzyl dimethyl ketal.
  • the alkylphenone compound is preferably the compound having a partial structure represented by formula (d2) from the viewpoint of sensitivity.
  • triazine compound examples include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-
  • acylphosphine oxide compound examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide.
  • Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF Corporation) may be used.
  • biimidazole compound examples include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (for example, see Japanese Patent Laid-Open No. H6-75372 and Japanese Patent Laid-Open No.
  • examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrene quinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and a titanocene compound. These are preferably used in combination with a polymerization initiation aid (D1)
  • Examples of a polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfoniumhexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfoniumhexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodoniumhexafluoroantimonate; nitrobenzyl tosylates; and benzoin tosylates.
  • onium salts such as 4-hydroxyphenyldimethylsulfonium p
  • the polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.
  • the content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass or less, and more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C).
  • the content of the polymerization initiator (D) falls within the above-mentioned range, there is a tendency that the sensitivity is increased and the time of exposure to light is shortened, resulting in the improvement in productivity of the color filter.
  • the polymerization initiation aid (D1) is a compound to be used for accelerating polymerization of a polymerizable compound, the polymerization of which has been started by the polymerization initiator, or a sensitizer. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D).
  • Examples of the polymerization initiation aid (D1) include an amine compound, an alkoxyanthracene compound, a thioxanthone compound, and a carboxylic acid compound.
  • Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (common name: Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone.
  • 4,4'-bis(diethylamino)benzophenone is preferable.
  • Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.
  • alkoxyanthracene compound examples include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.
  • Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.
  • carboxylic acid compound examples include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenysulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.
  • the content thereof is preferably 0.1 parts by mass or more and 30 parts by mass or less, and more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C).
  • the amount of the polymerization initiation aid (D1) falls within the above-mentioned range, there is a tendency that the colored pattern can be formed with higher sensitivity, resulting in the improvement in productivity of the color filter.
  • the solvent (E) is not particularly limited, and any solvent that has been used conventionally in the art can be used.
  • the solvent (E) include an ester solvent (a solvent that contains -COO- but does not contain -O- in its molecule), an ether solvent (a solvent that contains -O-but does not contain -COO- in its molecule), an ether ester solvent (a solvent that contains -COO- and -O- in its molecule), a ketone solvent (a solvent that contains -CO- but does not contain -COO- in its molecule), an alcohol solvent (a solvent that contains OH but does not contain -O-, -CO-nor -COO- in its molecule), an aromatic hydrocarbon solvent, an amide solvent, and dimethyl sulfoxide.
  • an ester solvent a solvent that contains -COO- but does not contain -O- in its molecule
  • an ether solvent a solvent that contains -O-but does not contain -COO- in its molecule
  • ester solvent examples include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxy isobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and ⁇ -butyrolactone.
  • ether solvent examples include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, and methyl anisole.
  • ether ester solvent examples include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxy propionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monoethyl ether
  • ketone solvent examples include 4-hydroxy-4-methyl-2-pentanone (that is, diacetone alcohol), acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.
  • alcohol solvent examples include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.
  • aromatic hydrocarbon solvent examples include benzene, toluene, xylene, and mesitylene.
  • amide solvent examples include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
  • the solvent is preferably a solvent containing at least one selected from the group consisting of propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4-methyl-2-pentanone, and N,N-dimethylformamide, and more preferably a solvent containing at least one selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, ethyl 3-ethoxypropionate, and 4-hydroxy-4-methyl-2-pentanone.
  • the content of the solvent (E) is preferably 55% by mass or more and 95% by mass or less, and more preferably 60% by mass or more and 92% by mass or less, relative to the whole amount of the colored composition of the present invention.
  • the content of the solid content of the colored composition is preferably 5% by mass or more and 45% by mass or less, and more preferably 8% by mass or more and 40% by mass or less.
  • leveling agent (F) examples include a silicone-based surfactant, a fluorine-based surfactant, and a silicone-based surfactant having a fluorine atom. These may have a polymerizable group at its side chain.
  • silicone-based surfactant examples include a surfactant having a siloxane bond in its molecule.
  • Specific examples thereof include Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, and Toray Silicone SH8400 (trade name; manufactured by Toray Dow Corning Co., Ltd.); KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.); and TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Inc.).
  • fluorine-based surfactant examples include a surfactant having a fluorocarbon chain in its molecule. Specific examples thereof include Fluorad (registered trademark) FC430 and Fluorad FC431 (manufactured by Sumitomo 3M, Ltd.); Megafac (registered trademark) F142D, Megafac F171, Megafac F172, Megafac F173, Megafac F177, Megafac F183, Megafac F554, Megafac R30, and Megafac RS-718-K (manufactured by DIC Corporation); Eftop (registered trademark) EF301, Eftop EF303, Eftop EF351, and Eftop EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.); Surflon (registered trademark) S381, Surflon S382, Surflon SC101, and Surflon SC105 (manufactured by AGC Inc.); and E5844 (
  • silicone-based surfactant having a fluorine atom examples include a surfactant having a siloxane bond and a fluorocarbon chain in its molecule. Specific examples thereof include Megafac (registered trademark) R08, Megafac BL20, Megafac F475, Megafac F477, and Megafac F443 (manufactured by DIC Corporation).
  • the content of the leveling agent (F) is preferably 0.00001% by mass or more and 0.2% by mass or less, more preferably 0.00002% by mass or more and 0.1% by mass or less, and still more preferably 0.0001% by mass or more and 0.05% by mass or less, relative to the whole amount of the colored composition. This content does not include the content of the pigment dispersant.
  • the content of the leveling agent (F) falls within the above-mentioned range, the flatness of the color filter can be improved.
  • the colored composition may contain an additive known in the art, such as a filler, other polymeric compounds, an adhesion promoter, an antioxidant, a light stabilizer, or a chain transfer agent.
  • an additive known in the art, such as a filler, other polymeric compounds, an adhesion promoter, an antioxidant, a light stabilizer, or a chain transfer agent.
  • the colored composition can be prepared by, for example, mixing a colorant (A) and a resin (B), as well as a polymerizable compound (C), a polymerization initiator (D), a solvent (E), a leveling agent (F), and other components to be used if necessary.
  • the mixing can be performed using a known or commonly used device under known or commonly used conditions.
  • the colorant (A) may be mixed with a part or the whole of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size reaches about 0.2 ⁇ m or less. In this operation, a part or the whole of the dispersant and the resin (B) may also be blended therewith, if necessary.
  • the dispersion liquid thus obtained is preferably mixed with the remaining components such that predetermined concentrations are attained to prepare a desired colored composition.
  • beads When using a bead mill, beads preferably have a diameter of 0.05 mm or more and 0.5 mm or less and may be made of glass, ceramic, metal, or the like.
  • Examples of the method for producing a colored pattern of a color filter from the colored composition of the present invention include a photolithography method, an inkjet method, and a printing method.
  • a photolithography method is preferable.
  • the photolithography method is a method in which the colored composition is applied onto a substrate and then dried to form a composition layer, and the composition layer is then developed by exposing the composition layer to light through a photomask.
  • a colored coating film which is a cured material of the composition layer, can be formed when the photomask is not used during the exposure to light and/or the composition layer is not developed.
  • the film thickness of the color filter (cured film) is not particularly limited, and may be selected appropriately depending on the purpose and application.
  • the film thickness thereof is, for example, 0.1 ⁇ m or more and 30 ⁇ m or less, preferably 0.1 ⁇ m or more and 20 ⁇ m or less, more preferably 0.5 ⁇ m or more and 6 ⁇ m or less.
  • the substrate to be used examples include glass substrates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass of which the surface is coated with silica; resin substrates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and a substrate obtained by forming thin film of an aluminum, silver, or a silver/copper/palladium alloy or the like on any of the aforementioned substrates. On such a substrate, another color filter layer, a resin layer, a transistor, a circuit, and the like may be formed. A substrate obtained by subjecting a silicon substrate to HMDS treatment may also be used.
  • glass substrates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass of which the surface is coated with silica
  • resin substrates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate
  • silicon silicon
  • each color pixel by a photolithography method can be carried out using a known or conventional device under known or conventional conditions.
  • the color pixel can be prepared in the following manner. First, a colored composition is applied onto a substrate, and then dried by heat-drying (prebaking) and/or drying under reduced pressure to remove volatile components such as a solvent from the composition, thereby producing a smooth composition layer. Examples of the application method include a spin coat method, a slit coat method, and a slit-and-spin coat method.
  • the temperature at heat-drying is preferably 30°C or higher and 120°C or lower, and more preferably 50°C or higher and 110°C or lower.
  • the time for the heating is preferably 10 seconds or more and 60 minutes or less, and more preferably 30 seconds or more and 30 minutes or less.
  • the drying procedure is preferably carried out at a temperature range of 20 to 25°C under a pressure of 50 to 150 Pa.
  • the film thickness of the composition layer is not particularly limited, and may be selected appropriately depending on the desired film thickness of the color filter.
  • the composition layer is exposed to light through a photomask for forming a desired colored pattern.
  • the pattern on the photomask is not particularly limited, and a pattern suitable for the intended application is used.
  • a light source to be used for the exposure to light is preferably a light source capable of generating light having a wavelength of 250 to 450 nm. For example, light having a wavelength of shorter than 350 nm may be cut with a filter capable of cutting light having this wavelength region, or light having a wavelength of around 436 nm, around 408 nm, or around 365 nm may be extracted selectively with a band-pass filter capable of extracting light having those wavelength regions.
  • the light source include a mercury lamp, a light-emitting diode, a metal halide lamp, and a halogen lamp.
  • a reduction projection exposure apparatus such as a mask aligner and a stepper, or a proximity exposure apparatus is preferably used because these apparatuses are capable of emitting a parallel light beam uniformly over the whole area of the exposed surface or accurately aligning the photomask to the substrate.
  • a colored pattern is formed on the substrate by bringing the exposed composition layer into contact with a developing solution to develop the composition layer.
  • the developing solution is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide.
  • the concentration of the alkaline compound in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, and more preferably 0.03% by mass or more and 5% by mass or less.
  • the developing solution may further contain a surfactant.
  • the developing method may be any of a paddle method, a dipping method, a spray method, and the like. Furthermore, during the developing process, the substrate may be inclined at any angle.
  • the resultant product is preferably washed with water.
  • the resultant colored pattern is preferably subjected to post-baking.
  • the temperature for the post-baking is preferably 80°C or higher and 250°C or lower, and more preferably 100°C or higher and 245°C or lower.
  • the time for the post-baking is preferably 1 minute or more and 120 minutes or less, and more preferably 2 minutes or more and 30 minutes or less.
  • the colored pattern and the colored coating film thus produced are useful as a color filter.
  • the color filter is useful as a color filter used for a display device such as a liquid crystal display device or an organic EL device; an electronic paper; a solid-state image sensor; and the like.
  • a compound represented by formula (a) was produced according to the method described in Japanese Patent Laid-Open No. 2002-179979 .
  • a compound represented by formula (x1) was produced according to the method described in Japanese Patent Laid-Open No. 2015-61907 .
  • a proper amount of nitrogen was passed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen. Then, 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added into the flask, and then heated to 85°C while stirring.
  • the solution was retained at the same temperature for 4 hours, and then cooled to room temperature to obtain a copolymer (resin B-1) solution having a solid content of 25.6%.
  • the produced copolymer had a weight average molecular weight (Mw) of 8000, a degree of dispersion of 2.1, and an acid value of 111 mg-KOH/g in terms of solid content.
  • the resin B-1 has the following structural units.
  • a proper amount of nitrogen was passed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen. Then, 280 parts of propylene glycol monomethyl ether acetate was added into the flask, and then heated to 80°C while stirring.
  • the solution was retained at 80°C for 4 hours, and then cooled to room temperature to obtain a copolymer (resin B-2) solution having a solid content of 35.1% and a viscosity of 125 mPas as measured at 23°C with a Type-B viscometer.
  • the produced copolymer had a weight average molecular weight (Mw) of 9.2 ⁇ 10 3 , a degree of dispersion of 2.08, and an acid value of 77 mg-KOH/g in terms of solid content.
  • the resin B-2 has the following structural units.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured using the GPC method under the following conditions.
  • the dispersion (P), colorant (x1), resin (B), polymerizable compound (C), polymerization initiator (D), solvent (E), and leveling agent (F) were mixed such that the composition shown in Table 8 was attained to prepare a colored composition.
  • each component represents the following compounds.
  • the colored composition prepared in each of Examples 1 to 9 and Comparative Example 1 was applied by a spin coating method and then pre-baked at 100°C for 3 minutes to form a colored composition layer. After being allowed to cool, the colored composition layer was irradiated with light without a photomask using an exposure machine (TME-150RSK manufactured by Topcon Corporation) in ambient atmosphere at an exposure dose of 60 mJ/cm 2 (365 nm standard). The colored composition layer that had been irradiated with light was post-baked in an oven at 230°C for 20 minutes to obtain a colored coating film. After being allowed to cool, the film thickness of the obtained colored coating film was measured using a film thickness measurement device (DEKTAK3 manufactured by Japan Vacuum Engineering Co., Ltd.).
  • the obtained colored coating film was subjected to spectrometry with a colorimeter (OSP-SP-200 manufactured by Olympus Corporation), and xy chromaticity coordinates (x, y) and tristimulus value Y in the CIE-XYZ color system were measured using the characteristic function for a C light source.
  • OSP-SP-200 manufactured by Olympus Corporation
  • xy chromaticity coordinates (x, y) and tristimulus value Y in the CIE-XYZ color system were measured using the characteristic function for a C light source.
  • UV ashing resistance was evaluated by irradiating the obtained colored coating film with UV of 2000 mW/cm 3 using an ultraviolet ozone cleaner (UV-312 manufactured by Technovision, inc.).
  • UV-312 manufactured by Technovision, inc.
  • the xy chromaticity coordinates (x, y) and Y were measured before and after the irradiation, and the color difference ⁇ Eab* was calculated from the measurement values by the method described in JIS Z 8730:2009 (7. Method for calculating color difference).
  • the results are shown in Table 9.
  • a smaller ⁇ Eab* value means that the degree of change in color is smaller.
  • the colored coating film having ⁇ Eab* of 5 or less can be practically used as a color filter without any problem.
  • the colored composition of the present invention can form a color filter having excellent UV ashing resistance.

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  • Chemical & Material Sciences (AREA)
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  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
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  • Plural Heterocyclic Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
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  • Optical Filters (AREA)
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AT320064B (de) 1971-09-17 1975-01-27 Ludwig Ludin Dipl Ing Stator für Elektroumlaufmaschine
DE3412730A1 (de) * 1984-04-05 1985-10-17 Hoechst Ag, 6230 Frankfurt Disazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung
JPH0651737B2 (ja) 1986-01-27 1994-07-06 東洋紡績株式会社 感光性組成物
JPH077198B2 (ja) * 1986-07-22 1995-01-30 富士写真フイルム株式会社 ハロゲン化銀写真感光材料の処理方法
JPH0675372A (ja) 1992-08-28 1994-03-18 Toppan Printing Co Ltd 感光性着色組成物およびカラーフィルターの製造方法およびカラーフィルター
JPH0675373A (ja) 1992-08-28 1994-03-18 Toppan Printing Co Ltd 感光性着色組成物およびカラーフィルターの製造方法およびカラーフィルター
JP3365434B2 (ja) 1993-06-22 2003-01-14 三菱化学株式会社 光重合性組成物及び感光材料
JP2002179979A (ja) 2000-10-05 2002-06-26 Toray Ind Inc カラーペースト、カラーフィルターおよび液晶表示パネル
TWI456345B (zh) 2008-06-03 2014-10-11 Sumitomo Chemical Co 著色硬化性組成物
CN103087544A (zh) * 2011-11-07 2013-05-08 南京工业大学 一种对苯二胺系双偶氮有机颜料及其制备方法
WO2013090771A1 (fr) * 2011-12-14 2013-06-20 The Trustees Of Dartmouth College Dérivés de triazolium et de tétrazolium comme émetteurs de lumière organique
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